Dempsey Hill Holiday Rentals, Singapore: Private House Rentals

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Go beyond your typical stay in Dempsey Hill

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Our top choices for Dempsey Hill hotels

A Holiday Inn Express building with a modern glass facade, a covered entrance, and a landscaped area with trees and shrubs.

A long swimming pool with a cityscape in the background.

A modern building with multiple floors, large windows, and a rooftop garden with seating areas.

A modern reception desk with a wooden panel wall, a staircase, and red chairs.

1. Holiday Inn Express Singapore Clarke Quay by IHG

Downtown Singapore

Yong

฿4,949

฿6,154 total

includes taxes & fees

7 Nov - 8 Nov

A spacious lobby with a central water feature, surrounded by seating areas and large windows.

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge areas.

A multi-level atrium with balconies covered in greenery, a central open space, and a view of the sky.

A spacious lobby with high ceilings, large columns, and a central seating area with sofas and a small water feature.

2. Shangri-La Singapore

Central Singapore

Maria

฿8,463

฿10,147 total

includes taxes & fees

31 Oct - 1 Nov

A bar area with a long counter, bar stools, and a bartender preparing drinks.

A lush indoor garden with multiple water features and dense foliage.

A lush indoor garden with a pathway leading to a seating area with wicker furniture and white cushions.

A serene outdoor pool area with a water feature, surrounded by lush greenery and modern seating.

3. Grand Hyatt Singapore

Orchard

Laurie

฿9,950

฿11,930 total

includes taxes & fees

16 Oct - 17 Oct

A tall hotel with a curved facade, illuminated signage, and a prominent 'Carlton' sign at the top.

A hotel room with a large bed, a desk, a chair, a TV, a bathroom with a bathtub, and a view of the city.

An outdoor seating area with tables, chairs, and a sofa, surrounded by large potted plants and wooden slats.

A spacious lobby with a central seating area, a reception desk, and a decorative chandelier.

4. Carlton Hotel Singapore

Central Singapore

Joseph Oluwafemi

฿6,227

฿7,467 total

includes taxes & fees

18 Oct - 19 Oct

A modern dining area with a long wooden table, multiple chairs, and a bar in the background.

A modern conference room with a long table, chairs, and a projector.

A high-rise hotel with multiple floors, a prominent entrance, and a modern architectural design.

5. YOTEL Singapore Orchard Road

Orchard

Lily

฿4,324

฿5,185 total

includes taxes & fees

19 Oct - 20 Oct

A hotel with multiple floors, a swimming pool, and outdoor seating areas.

A modern lobby with a central seating area, a staircase, and a wall with greenery.

A modern restaurant with high ceilings, pendant lighting, and a central bar area.

A modern hotel room with a sofa, armchair, ottoman, and a bed.

6. JEN Singapore Tanglin by Shangri-La

Orchard

Maricel

฿4,845

฿5,809 total

includes taxes & fees

1 Nov - 2 Nov

A hotel pool area with multiple lounge chairs and a swimming pool.

A spacious hotel lobby with multiple seating areas, a reception desk, and a view of the city through large windows.

A reception area with a dark wooden reception desk, a person standing behind it, and a lamp on the left.

A hotel room with a bed, a desk with a chair, a small table with a bowl of fruit, a lamp, and a TV on the wall.

7. York Hotel

Orchard

ALI

฿4,360

฿5,228 total

includes taxes & fees

1 Nov - 2 Nov

The exterior of the Voco An IHG Hotel with a distinctive bird sculpture in the entrance.

A dining area with a long table set for a meal, large windows offering a city view, and modern interior design.

A modern living room with a large window, a sofa, a coffee table, and a chair.

An outdoor dining area with tables and chairs, a bar with shelves of bottles, and a view of the cityscape at dusk.

8. voco Orchard Singapore by IHG

Orchard

Darren Richard

฿7,122

฿8,540 total

includes taxes & fees

6 Nov - 7 Nov

A rooftop pool with lounge chairs and a city skyline view.

An outdoor dining area with tables and chairs, a city skyline view, and a covered roof structure.

The entrance of the Hilton Garden Inn with a large circular sculpture and the hotel's name displayed prominently.

A modern hotel lobby with a marble reception desk, black chairs, and a view of the cityscape through large windows.

9. Hilton Garden Inn Singapore Serangoon

Little India

Dirk

฿4,445

฿5,329 total

includes taxes & fees

5 Nov - 6 Nov

A rooftop lounge with lounge chairs and a glass balustrade overlooking a cityscape.

An outdoor dining area with wicker chairs and a wooden table, surrounded by lush greenery and a small pond.

A modern restaurant with a bar area, red and grey chairs, and a view of greenery through large windows.

A modern hotel with a prominent 'quintet' sign, featuring a grid of balconies, large windows, and a mix of glass and brown facade.

10. Quincy Hotel Singapore by Far East Hospitality

Central Singapore

Deeksha

฿5,676

฿6,805 total

includes taxes & fees

31 Oct - 1 Nov

A buffet setup with various food containers and utensils.

A gym with treadmills, weight machines, and free weights.

A modern reception desk with a wooden finish, a glass display case with various bottles, and a digital kiosk.

A modern hotel with a glass facade, a visible entrance, and a sign for 'Holiday Inn Express'.

11. Holiday Inn Express Singapore Orchard Road by IHG

Orchard

Mohamed

฿6,075

฿7,598 total

includes taxes & fees

9 Nov - 10 Nov

A spacious lobby with a grand staircase, a reception desk, and a decorative chandelier.

A buffet area with seafood, salads, and various dishes.

A modern hotel room with a living area, a dining table, a sofa, and a TV.

A hotel room with a bed, a TV mounted on the wall, a small table with a remote control, and a yellow chair.

12. Royal Plaza on Scotts

Orchard

Kurt Wei

฿6,481

฿7,770 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

A modern hotel entrance with a prominent 'Alloft Hotels' sign, a large illuminated sculpture, and a spacious entrance area.

A modern breakfast bar with a variety of food options, a coffee machine, and a fruit display.

A modern hotel with a large swimming pool, palm trees, and high-rise buildings in the background.

13. Aloft by Marriott Singapore Novena

Central Singapore

Pankaj

฿4,897

฿5,871 total

includes taxes & fees

30 Oct - 31 Oct

A hotel room with a bed, a desk, a wardrobe, and a large window with a cityscape view.

A bar area with a marble counter, multiple bar stools, and a television screen.

A compact kitchenette with a small refrigerator, a coffee maker, and a drawer with various items.

A tall, modern building with a grid of windows and a red trim at the top.

14. ibis Singapore On Bencoolen

Central Singapore

Yukiko

฿3,797

฿4,552 total

includes taxes & fees

1 Nov - 2 Nov

A high-rise hotel with a prominent Grand Cypress sign, reflecting in the water.

A buffet with a variety of dishes and a scenic view through large windows.

A hotel room with two beds, a sitting area, and a view of a cityscape at night.

A breakfast table with various dishes and drinks, a coffee pot, and a view of a cityscape through large windows.

15. Grand Copthorne Waterfront Hotel Singapore

Central Singapore

LaKica

฿5,237

฿6,279 total

includes taxes & fees

8 Nov - 9 Nov

A rooftop infinity pool with green seating and red umbrellas, overlooking a city skyline.

A modern hotel room with a city view, a sofa set, yellow chairs, and a large window.

A person dining at an outdoor table with a city skyline in the background.

A room with a large window overlooking a cityscape at sunset.

16. JEN Singapore Orchardgateway by Shangri-La

Orchard

Ami

฿6,808

฿8,163 total

includes taxes & fees

1 Nov - 2 Nov

A hotel with a prominent 'Orchard Rendezvous Hotel' sign, large windows, and a modern architectural design.

A bar area with high stools, a bar counter, and shelves with bottles and glasses.

A spacious lobby with a high ceiling, a large tree, and multiple seating areas.

A hotel room with a large bed, a desk with a laptop, a chair, a small table with a plant, and a large window with a view.

17. Orchard Rendezvous Hotel by Far East Hospitality

Orchard

Nobumori

฿5,564

฿6,672 total

includes taxes & fees

24 Oct - 25 Oct

A multi-level atrium with a central open space surrounded by seating areas and staircases.

A spacious lobby with a modern design, featuring a central seating area with sofas and a staircase leading to upper levels.

A bar area with stools, a counter, and shelves of bottles.

A modern hotel entrance with a glass facade, a fountain, and a landscaped area with steps leading up to the entrance.

18. Holiday Inn Singapore Atrium by IHG

Central Singapore

HARRY

฿4,556

฿5,463 total

includes taxes & fees

8 Nov - 9 Nov

A modern hotel lobby with high ceilings, a central seating area, and a reception desk.

A modern hotel with a prominent Hilton sign, surrounded by high-rise buildings and a busy urban street at dusk.

A modern outdoor pool area with lounge chairs and umbrellas, surrounded by a vertical garden and a contemporary building facade.

A modern hotel lobby with a central potted plant, geometric light fixtures, and a clean, minimalist design.

19. Hilton Singapore Orchard

Orchard

Benjamin

฿8,159

฿9,783 total

includes taxes & fees

25 Oct - 26 Oct

A rooftop pool with lounge chairs and a table, surrounded by modern buildings and greenery.

A covered outdoor seating area with wicker furniture and yellow cushions, surrounded by greenery and modern buildings in the background.

A modern reception area with a marble reception desk, a wheelchair accessibility sign, and a view of the city through a glass wall.

A modern hotel with a glass facade, a rooftop garden, and a riverside location.

20. Hotel Boss

Kallang

Joann

฿2,968

฿3,559 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Dempsey Hill attractions

Lotto Carpets Gallery

You can spend an afternoon studying the exhibits at Lotto Carpets Gallery in Dempsey Hill. Wander through the picturesque gardens and marina in this vibrant area.

See properties

Learn more about Dempsey Hill

This former British military base now houses upscale restaurants and boutiques in lush, colonial-era buildings. Enjoy brunch at PS.Cafe before exploring the art galleries and speciality shops that fill the tranquil hilltop enclave.

See all hotels in Dempsey Hill

A covered outdoor seating area with ceiling fans, tables, and chairs.

Top Dempsey Hill Hotel Reviews

lyf Bugis Singapore

10/10 Excellent

"This hotel is close to everything such as restaurants, bars, mall, markets and more. MRT is outside the Bugis Junction with 2 stops and you’ll be in Marina Bay sand shopping. 12 minutes walk to the National Singapore Museum. The room is tiny but enough for just myself. Quite expensive for 5 night in a small room but I guess it’s because of the Formula One The staff were great and friendly . There is a bar/restaurant inside the hotel which it’s nice. Walking distance to everything. Thank you 🙏"

JEN Singapore Orchardgateway by Shangri-La

10/10 Excellent

"We love everything about Jen Orchard Gateway, from the location and amenities, to the friendly staff, amazing pool and great food. This was our 6th visit and we will be back again!"

Crowne Plaza Changi Airport by IHG

10/10 Excellent

"We thoroughly enjoyed our stay! Incredible views, lovely staff, and so conveniently placed within the airport. We will be staying here after every long haul flight going forward. Thank you for an incredible stay !"

Hotel Waterloo Singapore - Handwritten Collection

8/10 Good

"The location is very handy and the staff super friendly. The room was tiny but the mattresses were good and firm and the hotel was fairly quiet. They could provide more tea and coffee in the room though. For two people we only found one tea bag of green tea and one black tea, respectively, and we had to ask for more repetitively."

Carlton Hotel Singapore

10/10 Excellent

"Perfect room on the top floor. Great breakfast, typical for Asian countries. Had a swim in the pool, very clean and relaxing."

Dusit Thani Laguna Singapore

10/10 Excellent

"Great"

Marina Bay Sands

10/10 Excellent

"The most extraordinary stay I’ve had. Staff were amazing and their hospitality is top tier. All of the hotel concierge were helpful but when I was facing a huge difficulty with my credit card the front desk agent really put herself in my place and not only understood my problem but solved it. I cannot thank the marina bay sands team for taking care of me during my stay. I am definitely gonna be coming back. Everything was just divine."

Grand Park City Hall

8/10 Good

"Check in is a bit of a nightmare. Turned up at 1430 and didn’t get my room till 1630. Other than that was lovely"

More cheap stays in Dempsey Hill

The Quay Hotel Little India

195 Serangoon Rd Singapore

฿2,328

฿2,792 total

27 Oct - 28 Oct

includes taxes & fees

7/10 Good! (64 reviews)

Hmlet Essentials Novena

471 Balestier Rd Singapore

฿2,490

฿2,985 total

15 Oct - 16 Oct

includes taxes & fees

8.2/10 Very good! (127 reviews)

BEAT. Arts Hostel Chinatown

211A, South Bridge Road Singapore

฿2,879

฿3,167 total

26 Oct - 27 Oct

includes taxes & fees

6.4/10 (108 reviews)

KINN Habitat

5 Hongkong St Singapore

฿3,156

฿3,784 total

14 Oct - 15 Oct

includes taxes & fees

9.2/10 Wonderful! (201 reviews)

Beverly Hotels Elements

48 Horne Rd Singapore Singapore

฿3,394

฿4,069 total

12 Oct - 13 Oct

includes taxes & fees

8.4/10 Very good! (133 reviews)

Ambassador Transit Hotel Terminal 2

Singapore Changi Airport, PTB2 Singapore

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Frequently asked questions

Where is the best place to stay in Dempsey Hill?

Located 3.5 mi (5.6 km) from the heart of Dempsey Hill, Pan Pacific Singapore is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are JEN Singapore Tanglin by Shangri-La and Carlton Hotel Singapore. See all available top hotels, or vacation rentals in Dempsey Hill.

If I need to cancel my hotel reservation in Dempsey Hill, will I receive a refund?

Yes! The majority of room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Dempsey Hill.

How is it to stay in Dempsey Hill?

Visitors can enjoy all that Dempsey Hill has to offer, including the gardens, shopping and restaurants. Tourists can also enjoy the city's football games and bars. Orchard Road, Universal Studios Singapore and Marina Bay Sands Casino are some of the top sights around the area. There are 793 hotels and other accommodation options in the surrounding area. Find out more about Dempsey Hill.

What is there to see in Dempsey Hill?

A favourite place to visit is Lotto Carpets Gallery. You'll also find Orchard Road and Universal Studios Singapore in the area. Take a look at what more there is to see and do in Expedia's Dempsey Hill guide.

What's the seasonal weather like in Dempsey Hill?

The hottest months are usually May and April, with an average temperature of 28°C, while the coldest months are January and February, with an average of 27°C. The rainiest months in Dempsey Hill are November, December, October and April, with each month seeing an average of 321 mm of rainfall.

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Book Hotels in Dempsey Hill on Expedia.com.sg

Find hotels in Dempsey Hill from ฿2,792

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Dempsey Hill

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Dempsey Hill hotels

1. Holiday Inn Express Singapore Clarke Quay by IHG

2. Shangri-La Singapore

3. Grand Hyatt Singapore

4. Carlton Hotel Singapore

5. YOTEL Singapore Orchard Road

6. JEN Singapore Tanglin by Shangri-La

7. York Hotel

8. voco Orchard Singapore by IHG

9. Hilton Garden Inn Singapore Serangoon

10. Quincy Hotel Singapore by Far East Hospitality

11. Holiday Inn Express Singapore Orchard Road by IHG

12. Royal Plaza on Scotts

13. Aloft by Marriott Singapore Novena

14. ibis Singapore On Bencoolen

15. Grand Copthorne Waterfront Hotel Singapore

16. JEN Singapore Orchardgateway by Shangri-La

17. Orchard Rendezvous Hotel by Far East Hospitality

18. Holiday Inn Singapore Atrium by IHG

19. Hilton Singapore Orchard

20. Hotel Boss

Stay near popular Dempsey Hill attractions

Lotto Carpets Gallery

Learn more about Dempsey Hill

Top Dempsey Hill Hotel Reviews

lyf Bugis Singapore

JEN Singapore Orchardgateway by Shangri-La

Crowne Plaza Changi Airport by IHG

Hotel Waterloo Singapore - Handwritten Collection

Carlton Hotel Singapore

Dusit Thani Laguna Singapore

Marina Bay Sands

Grand Park City Hall

More cheap stays in Dempsey Hill

The Quay Hotel Little India

Hmlet Essentials Novena

BEAT. Arts Hostel Chinatown

KINN Habitat

Beverly Hotels Elements

Ambassador Transit Hotel Terminal 2

Frequently asked questions

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